'Gangs of New York'

When: 2002
Co-stars: Cameron Diaz and Daniel Day-Lewis
What: Collaborating with Martin Scorsese for the first time in "Gangs of New York," Leo starred as Amsterdam Vallon, who returns to the Five Points seeking revenge against Bill the Butcher (Daniel Day-Lewis), his father's killer.

'The Departed'

When: 2006
Co-stars: Matt Damon and Jack Nicholson
What: Teaming up with director Martin Scorsese for the third time ("Gangs of New York" and "The Aviator"), DiCaprio was praised for his performance as Billy, a Massachusetts State Police officer who goes undercover to take down a crime boss.
The film won several Academy Awards for Best Picture, Best Director, Best Adapted Screenplay and Best Film Editing.

'Blood Diamond'

When: 2006
Co-stars: Djimon Hounsou and Jennifer Connelly
What: Leonardo was nominated for Best Actor in his role as Danny Archer -- who gets involved the dangerous blood diamond crisis in Sierra Leone.
Archer offers to help Solomon (Djimon Hounsou) find his lost family, as long as Solomon agrees to lead him to an enormous diamond he discovered.
In addition to his riveting performance, Leo's South African accent was quite impressive!

'Revolutionary Road'

When: 2008
Co-stars: Kate Winslet
What: In their second film together, Kate Winslet and Leo played Frank and April Wheeler, a married couple who struggle to come to terms with their problems, while trying to raise two kids.
Although he was nominated for a Golden Globe, DiCaprio did not win. Kate, however, took home a Globe for Best Actress in a leading role.

'Inception'

When: 2010
Co-stars: Joseph Gordon-Levitt and Ellen Page
What: Hailed as one of 2010's most visually stunning films with an equally intense storyline, Leo plays master "dream thief" Dom Cobb-who assembles his crew and goes in for his final job. But was it all just a dream?